The Catalyst by Softchoice

The Curiosity Episode: You're Not What You Know

• Softchoice • Season 7 • Episode 11

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0:00 | 24:13

What got you here won't get you there. For most IT leaders, the path to the top was paved with expertise — knowing the systems, owning the decisions, having the answers. But something happens when that playbook stops working. Not a crash. Not a failure. Just a quiet plateau that tells you something needs to change.

In this episode of The Catalyst, we explore what's on the other side of that wall: a shift toward curiosity, empowerment, and a fundamentally different way of leading. Featuring leadership coach Kirsten Schmidtke, curiosity researcher Dr. Deb Clary, and Benevity VP of Engineering Rob Woolley — three voices who all landed in the same place.

What you'll take away:

  • Why expertise becomes a trap for senior IT leaders — and how to recognize when it's happening to you
  • The one behaviour change Rob Woolley made that created what he calls "titanic shifts" in his leadership
  • What MIT-commissioned research reveals about the direct link between curiosity and organizational performance
  • Why the best leaders aren't the ones with the most answers — and what they do instead

Featuring: Rob Woolley, VP Core Platform & Data Engineering at Benevity | Kirsten Schmidtke, Leadership Coach & Growth Advisor | Dr. Deb Clary, Author of The Curiosity Curve (Fast Company Press)

Learn more about Kirsten at kirstenschmidtke.com 

Take Deb's curiosity assessment at debraclary.com 

#ITLeadership #MidMarketIT #TheCatalyst #CuriousLeadership #Softchoice #LeadershipDevelopment #FutureOfIT


The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology. 

Tobin:

Producer Tobin here and before we jump into the show today, we do have a bit of an announcement and to help me make that announcement, I'm actually joined by Heather. Hey Heather.

Heather:

Hey Tobin.

Tobin:

So yeah, I was just doing my work today and I got a, a message from you over teams and that'd be important for our audience to be caught up. So why don't you tell us what the big news is.

Heather:

Absolutely. Thank you for giving me a moment to be able to do that. I wanted to say a big thank you to the listeners here. I've taken a new role, uh, so I'll be leaving Softchoice and that means that I'll be leaving the catalyst and I'm really grateful for the engagement and support that we've received from our listeners. It's really meant more to me than, you know, hearing from listeners about which episodes resonated, what insights that they've taken back to their teams, and how conversations have sparked new thinking. That's been the most rewarding part of this journey. So with that, I'm excited for what's ahead for the Catalyst. There are incredible episodes and conversations on the horizon, and I can't wait for you to experience them. Heather Haskin with the Catalyst signing off.

Katey:

A few years ago, Deb Clary was on a train from Rome to Florence. She'd spent decades in corporate America. Frito Lay, Coca-Cola, Jack Daniels rising from a root driver to the boardroom. She was by any measure, someone who had made it by knowing things. And then the man sitting next to her told a joke.

Deb:

And I was sitting next to an Italian man, a handsome Italian man, and he turns to me and says, are you American? And I said, why? Yes I am. He says, well, I have the best American joke. I go, what is it? He says, what do you get when you ask an American a question? Uh, I don't know. He starts laughing. He says, you get an answer.

Katey:

She didn't get it at first. She smiled and let it go, but it stayed with her because the more she thought about. The more she watched the conversations happening around her in Europe, actual dialogues, questions, building on questions, the more she realized the joke wasn't really about Americans, it was about expertise. And what happens when knowing the answer becomes the whole job.

Deb:

I began to notice that Europeans had different conversations than Americans. They were having a dialogue versus just answering a question.

Katey:

Around the same time on the other side of the world, a guy named Rob Woolley was sitting with his team at a SaaS company in Calgary, reviewing a year's worth of work, good work, solid numbers, no fires, no disasters, and he felt a knot in his stomach.

Rob:

We had a good year. We didn't have an impactful year. Okay, where's the intensity at? Ooh, the intensity is comfortable. That's usually just for my myself personally. That's usually a flag.

Katey:

A good year that didn't feel good. A career built on having the answers suddenly running out of road. Today's episode is about what happens next about the IT leaders who hit that wall and what they found on the other side of it. From Softchoice, a worldwide technology company. This is the catalyst. I'm Katie Tsing. This season we're doing things a bit differently. We're making audio documentaries. Real stories from the front lines of it, exploring the challenges of small teams chasing big dreams. Today's episode, what it really takes to lead when the old playbook stops working. We are calling it the curiosity episode. Act one, the Armor. Here's something nobody tells you when you're coming up in it. The thing that gets you promoted, the deep knowledge, the fast answers, the ability to walk into a room and just know that same thing will eventually work against you. Not because the knowledge stops being useful, but because somewhere along the way it stops being enough. Deb Clary has spent the last several years trying to explain why after four decades in corporate America. She started noticing a pattern in the leaders she worked with. They were technically excellent, they were experienced, and a surprising number of them were stuck.

Deb:

We go to the university and we become a software engineer or a medical doctor or a lawyer, and that expertise becomes our armor. And besides that, we're have time constraints. In my head, I think I don't have time to go. I don't have time to ask other people questions. I just need to execute because I'm the expert and I'm rewarded for that expertise.

Katey:

Rewarded for it. That's the thing. This isn't a story about bad habits. It's a story about good habits that stop scaling. Think about what IT leadership was built on and still is at a lot of organizations, protect the systems, own the decisions. When something breaks, fix it. When someone has a question, answer it, be the one who knows. That model worked. It kept the lights on. In a lot of cases it still does.

Deb:

The short game is an employee comes in, they have a problem, the leader tells 'em how to do that. Now we do that because it's efficient and because we probably think we have the answer.

Katey:

Rob Woolley spent 25 years building that kind of credibility, firmware, hardware, medical imaging, pipeline, SCADA systems. He had the kind of resume that makes younger engineers lean in when he starts talking and he knows it. He's been a VP of Core platform and data engineering at Benevity, a tech for good SaaS company based in Calgary for the last couple of years. Before that, he'd spent nearly a decade there building things, breaking things, and fixing them. The job he wanted was always the same. Drive, change, have impact, keep the machine running. For a long time it worked.

Rob:

Things got to a place where I'm like, ah, I feel like I'm maintaining. I don't feel like I'm driving. I, I like change that transformation. And I felt like I had hit this point where the style that I was using. Wasn't working to continue having a large impact.

Katey:

He didn't crash, he didn't burn out, he just leveled off. And for someone wired, the way Rob is wired, leveling off is its own kind of alarm.

Rob:

Leaders are, we are installed to control entropy. So whether that's chaos or complacency, like take your pick. Both are dangerous. We need to go in and address them. And so I was like, Ooh, we're getting complacent. I'm getting complacent. That's no good.

Katey:

He has this theory about comfort that for leaders, feeling comfortable is the canary in the coal mine. Not a reward, a warning.

Rob:

How comfortable you feel day to day. And I was like, Hey, this is cool. Yeah. You know, not, don't feel like I'm pushing all that hard. And that's, that's a big, it's a big no-no for me.

Katey:

Now, Rob is quick to point out that he's not the grumpy IT leader type. He has a teammate he loves who is. Someone who's been in the industry long enough to view most new technology with deep personal suspicion.

Rob:

I have this teammate that I've worked with on and off for years, and they're amazing. Uh, but they definitely fall into that grumpy archetype and, and I love them for it, and yet they always maintain. This like big spark of curiosity. So like as all the AI stuff is coming out, they're like, oh, AI slop, canons. I'm like, yeah, but you know, suddenly your game changing advantage of typing 130 words a minute has been taken away. And they're like, yeah, it's true.

Katey:

He says he loves the grumpy part. Somebody has to hold the line. But even that teammate, even the most committed skeptic in the room. Can feel the ground shifting. Rob had been feeling it for a while. He just didn't know yet what to do with it. He had what he calls borrowing from the Incredibles, the Mr. Incredible problem.

Rob:

You get that moment that you see in, uh, the Incredibles. Where Mr. Incredible is like, oh, I just saved the world. Can it say saved for like five minutes?

Katey:

The question wasn't whether Rob knew the answers he did. The question was whether knowing the answers was still the whole job. It wasn't Act two, the shift. Kirsten Schmidtke has a line she uses with clients that tends to land like a small grenade.

Kirsten:

My currency is no longer information. It's actually transformation, like, what do I do with that information? That's how we create change as leaders.

Katey:

Kirsten is a leadership coach based in Toronto. She started her career here at Softchoice, then spent years at Amazon Web Services before going out on her own. She works primarily with leaders in tech, people like Rob, and what she keeps seeing over and over is leaders who are incredibly good at one kind of currency and don't realize the exchange rate has changed.

Kirsten:

I really like to look at leadership as an identity shift that you need to now connect to new, a new identity. Like who are you being that thinks a certain way that does things in a certain way.'cause it actually starts with our state of being before we think, before we act, before we see the result

Katey:

and identity shift. Not a skills upgrade, not a management training course. Something harder and more personal than either of those. Kirsten sees this resistance all the time, particularly in leaders who built their credibility on technical depth. The shifts she's asking them to make can feel at first. Like giving something up

Kirsten:

so I can really understand where, you know, when we're so familiar with a way of working, of like having the answers, having the data, you know, knowing where to get the information and that having been our currency, it can feel really unfamiliar.

Katey:

Unfamiliar, that's a generous word for it. Rob would probably say uncomfortable. The change he made wasn't dramatic. He didn't overhaul his management style or start doing breathing exercises before all hands meetings. He made two adjustments, small ones that turned out not to be small at all,

Rob:

whenever there's a group conversation with, with any group, but in particular with our executive team. And if it's my time to jump in rather than maybe stating my position or my point of view, I'll just ask one more question. I definitely can very easily fall into that archetype of grumpy, know-it-all, and that's not in alignment with the identity that I wanna be, which is always curious.

Katey:

One more question. Before the answer every time. The second shift was about listening, which Rob like most people, thought he was already doing.

Rob:

I spent a great deal of time learning how to listen better and what I thought was active listening, and what active listening actually is. Were two very different things and that's been another, another game changer. I've become obsessed with the idea of earning the right to speak, so. You're chatting with somebody before you share your idea. Maybe you've asked all the questions you want to ask. It's like, oh, hold on. Let me make sure I got this, and rephrasing things back,

Katey:

earning the right to speak. It's a strange concept for someone who spent two and a half decades building the expertise that gave him the right to speak. But something happened when he started doing it.

Rob:

There was some very, I'll say subtle, other people would say Titanic shifts in communication style, which then started opening more doors.

Katey:

Titanic, his word, not mine. Deb Clary has seen this pattern play out in boardrooms across multiple industries. She became so interested in it. A few years ago, she commissioned a group of MIT researchers to test a hypothesis she'd been carrying since that train ride in Italy, that there's a measurable relationship between curiosity and leadership performance.

Deb:

Three months later, they came back and said. How'd you know there is a direct correlation between performance and curiosity?

Katey:

She now has a diagnostic tool, the curiosity curve, that measures curiosity across four dimensions, exploration, openness to new ideas. Inspirational creativity and focused engagement. She uses it with executive teams and sometimes the results are uncomfortable. She was running a two day strategy session with a company in trouble, revenue down, turnover up, products falling behind competitors. The CEO agreed a little reluctantly to have his whole leadership team take the assessment. 10 people. Their results were aggregated and displayed anonymously, just dots on a distribution chart. She pulled up the openness to new ideas. Dimension.

Deb:

Nine people scored extremely high openness to new ideas, and one individual scored low. And I said, now why would it be that you all are. You know, smart people, you all are coming in with these, seems like all these ideas, but they're not being executed. Long pause. And the CEO raised his hand and he said that low number is me. And he had this epiphany of I'm shutting down people. And eventually, you know, the company's gonna continue to lose money, but he's also gonna lose really good people. And within a year they completely turn the organization around.

Katey:

One moment of awareness, one CEO. Willing to say out loud what the data was already saying.

Deb:

When you're made aware of how you show up every day, you then have the opportunity to step into being different.

Katey:

Rob's version of that moment didn't happen in a strategy session. It happened in a harder room in late 2022. Benevity, like a lot of tech companies. Had to prepare for a reduction in force. These are never clean events. The IT team is almost always involved. Early badges, access accounts. The mechanics of someone's last day are in a lot of organizations. It's problem to manage. Rob had felt it coming. He'd been listening more, paying attention to signals in the business that a year earlier he might've missed. And when it became clear that this moment was going to arrive, he did something unusual. He taught his team to code, sort of.

Rob:

I worked with the team, this is right as chat, GBT was coming out, and I was like, listen, I'm gonna teach you how to code sort of. But I'm also gonna teach you how to use this thing to help you code, because I think we're gonna need to build some tools to automate how we're going to manage big changes in the workforce. And they're like, oh, okay. I'm like, let's just be ready. Like everybody's gonna have to do it at some point. Maybe we have to do it now.

Katey:

When the reduction in force came, the IT team was ready. No emails going out early. No badges deactivated before the conversations happened. No horror stories.

Rob:

People's first day should be as, as honorable and as caring as their last day.

Katey:

He said that quietly, like it was obvious. It's not obvious. Most organizations find this out the hard way

Rob:

because I had. Matured as a leader, and because we had great rapport with all of our partner groups and because the team was really tight and also very curious, we were able to pull together through a difficult event as smoothly as you possibly can.

Katey:

Act three, the new playbook. Here's a statistic that stopped me when I first heard it

Deb:

as children. We asked 298 questions a day. This was a group of neuroscience outta London that determined this. As adults, they say we ask about five,

Katey:

two hundred and ninety eight down to five. Something happens between being four years old and being 40. Some of it is school. Some of it is work. A lot of it Deb argues is reward systems. We get promoted for answers, not for questions, but here's the thing about it. Of all the industries where curiosity gets squeezed out, it might actually be one of the more natural homes for it because curiosity it turns out loves the same thing. It was built on

Deb:

creativity, loves constraints. And the same with curiosity. Curiosity loves constraints, and what are it people up against? They're up against deadline. They're up against rules and regulations, uh, keeping things safe. But at the same time, how do we do this differently? How do we do this better? How do we serve the the company in a different way?

Katey:

Kirsten Schmidtke talks about this in terms of what she calls zone of genius, the idea that the best leaders. Don't just develop their own curiosity, they create room for it in the people around them.

Kirsten:

An amazing leader is creating space for people to be at their best and to reach even higher potential. But we can't help people be their best if we don't know what they want or what they're great at,

Katey:

which requires first asking. And when leaders start asking, really asking, not as a management technique, but as a genuine practice, something changes in the room. Kirsten has a word for what unlocks when that happens.

Kirsten:

Simplicity scales, and we absolutely as human beings wanna overcomplicate everything.

Katey:

Simple questions. Ask consistently. That's the whole move.

Kirsten:

Discomfort is where growth is created, right? That's where as human beings, like our purpose is to grow, is to expand, is to experience more life. And the only way we can do that is by really adopting a growth mindset and. Getting out of our comfort zone, even if it's just just dipping our toes outside of it,

Katey:

dipping his toes, which is exactly what Rob would describe his version of this.

Kirsten:

Instead of telling their team, they're actually coaching their team, they're. Asking them questions to guide them to answers rather than telling them.

Deb:

When you answer a question, you've answered one question, but when you ask a series of questions to help that employee think, now you're developing a future leader.

Katey:

Rob came to this conclusion in his own way, the hard way, maybe through a plateau, through a reduction in force, through slowly unlearning the habit of being the smartest person in the room. At one point, talking to our producers, he brought up Jira. Jira 1.0 specifically.

Rob:

Oh, I used to know the ins and outs of Okta configuration. You don't need to anymore. And I remember Jira 1.0 and I, I've carried that like a badge of honor, and it's meaningless now because the LLMs will tell you how to configure Jira better than even I knew out.

Katey:

He mourned it briefly. All that accumulated knowledge suddenly less valuable than a well constructed prompt, and then something else happened.

Rob:

When I let go of that knowledge and then jumped on the facts, I'm like, oh, hold on. There was a whole new world to learn about.

Katey:

That's the trade. Let go of the badge of honor. Pick up the beginner's mind. Rob has a line he's landed on, that he uses with his team now and with people coming up behind him in the industry. It's simple. It's not particularly original, but the way he sees it. You can tell he actually believes it.

Rob:

You aren't what you know. You are what you're willing to learn. You are what you're willing to adapt to. And thi this one, like I said,

Katey:

he said that and then he kept talking because Rob always keeps talking and he ended up somewhere. I didn't expect.

Rob:

My favorite is when you're setting up MCP servers and command line utilities and you have to authorize into 10,000 things and put all these credentials into different spots. But at the end of the day, if, um, you know, the agent can successfully read your email and parse out your daughter's dance schedule and put it into the family calendar, you're like, I have, I have solved the most complicated problem in the world. Um, and those are great days.

Katey:

Three people, decades of combined experience and technology leadership, and the spaces where those two things collide. They all landed in the same place. The leaders who are thriving right now aren't the ones who found better answers. They're the ones who got better at asking questions

Rob:

to anybody who's feeling stuck. That'd be my big thing. He's just like, hold on, lich. You're not what you know, you're what you can learn.

Katey:

After his interview, Rob told our producers something about Kirsten that I think is worth putting on tape.

Rob:

I wish more people would reach out to her. I know I've recommended her to what feels like dozens of folks. I do wonder if there's, uh, it's a lot like therapy. I do wonder if many leaders feel that working with a coach or, or an expert like that is somehow a sign of failure or that they're not, not cut out for it. And that's, that's not the case. I, I wish I had done it sooner.

Katey:

If you want to find Kirsten, you can reach her@kirstenschmidtke.com or just find her on LinkedIn where she'll tell you the real conversations happen Anyway, and if you want to go deeper on the science behind all of this, the research, the framework, the four factors of the curiosity curve, Deb Cleary's book is out now from Fast Company Press. You can find it on Amazon or take her curiosity Assessment yourself@deborahclary.com. Here's the thing about curiosity. We can't give it to you and honestly, if you've made it this far into the episode, you probably don't need us to, but curiosity, without the right infrastructure, the right tools. The right partner who actually understands mid-market IT reality. That's just a good question with nowhere to go. Softchoice, a worldwide technology company works with more than 8,000 organizations across North America. They got there by asking the same questions. You're already asking about cloud, about ai, about how to do more with the team you actually have, and they know how to help you act on the answers. If you're ready to have that conversation, start@softchoice.com. The Catalyst was reported and produced by Tobin Dalrimple and the team at Pilgrim Content Editing by Ryan Clark With support from Philippe Demas, Joseph Beyer, and the marketing team at Softchoice. Special thanks to Rob Woolley, Kirsten Schmidtke and Dr. Deb Clary for sharing their stories and their thinking.